CA2644146C - Low molecular weight ampholytic polymers for personal care applications - Google Patents
Low molecular weight ampholytic polymers for personal care applications Download PDFInfo
- Publication number
- CA2644146C CA2644146C CA2644146A CA2644146A CA2644146C CA 2644146 C CA2644146 C CA 2644146C CA 2644146 A CA2644146 A CA 2644146A CA 2644146 A CA2644146 A CA 2644146A CA 2644146 C CA2644146 C CA 2644146C
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- CA
- Canada
- Prior art keywords
- hair
- weight percent
- reactor
- cosmetically acceptable
- monomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 229920000642 polymer Polymers 0.000 title claims abstract description 55
- 239000000203 mixture Substances 0.000 claims abstract description 130
- 239000000178 monomer Substances 0.000 claims abstract description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 24
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 23
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000002091 cationic group Chemical group 0.000 claims abstract description 22
- 125000000129 anionic group Chemical group 0.000 claims abstract description 19
- 239000003999 initiator Substances 0.000 claims abstract description 15
- 239000000126 substance Substances 0.000 claims abstract description 13
- 239000007787 solid Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 9
- 239000000872 buffer Substances 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000003352 sequestering agent Substances 0.000 claims abstract description 4
- 239000012986 chain transfer agent Substances 0.000 claims abstract description 3
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 238000010926 purge Methods 0.000 claims abstract description 3
- -1 aftershave Substances 0.000 claims description 67
- 239000004094 surface-active agent Substances 0.000 claims description 29
- 229920001296 polysiloxane Polymers 0.000 claims description 20
- 239000006210 lotion Substances 0.000 claims description 17
- 150000002191 fatty alcohols Chemical class 0.000 claims description 16
- 239000001993 wax Substances 0.000 claims description 16
- 235000019271 petrolatum Nutrition 0.000 claims description 12
- 239000004264 Petrolatum Substances 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- 229940066842 petrolatum Drugs 0.000 claims description 11
- 239000006071 cream Substances 0.000 claims description 10
- 239000012530 fluid Substances 0.000 claims description 10
- 239000003921 oil Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000002453 shampoo Substances 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 150000001412 amines Chemical group 0.000 claims description 9
- 239000000344 soap Substances 0.000 claims description 9
- 230000000475 sunscreen effect Effects 0.000 claims description 9
- 239000000516 sunscreening agent Substances 0.000 claims description 9
- 239000003974 emollient agent Substances 0.000 claims description 8
- 229920002545 silicone oil Polymers 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 150000002194 fatty esters Chemical class 0.000 claims description 7
- 239000003906 humectant Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 6
- 150000001720 carbohydrates Chemical class 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 238000004040 coloring Methods 0.000 claims description 6
- 229920013750 conditioning polymer Polymers 0.000 claims description 6
- YIOJGTBNHQAVBO-UHFFFAOYSA-N dimethyl-bis(prop-2-enyl)azanium Chemical class C=CC[N+](C)(C)CC=C YIOJGTBNHQAVBO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002480 mineral oil Substances 0.000 claims description 6
- 235000010446 mineral oil Nutrition 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 5
- 230000003745 detangling effect Effects 0.000 claims description 5
- 239000007921 spray Substances 0.000 claims description 5
- 241000195940 Bryophyta Species 0.000 claims description 4
- 235000010654 Melissa officinalis Nutrition 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 239000000865 liniment Substances 0.000 claims description 4
- 235000011929 mousse Nutrition 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000004851 dishwashing Methods 0.000 claims description 3
- 230000003370 grooming effect Effects 0.000 claims description 3
- 230000037308 hair color Effects 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 150000003904 phospholipids Chemical class 0.000 claims description 3
- 239000006254 rheological additive Substances 0.000 claims description 3
- 235000015961 tonic Nutrition 0.000 claims description 3
- 230000001256 tonic effect Effects 0.000 claims description 3
- 229960000716 tonics Drugs 0.000 claims description 3
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 2
- 150000002830 nitrogen compounds Chemical group 0.000 claims description 2
- 239000001024 permanent hair color Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000001027 temporary hair color Substances 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 241000021559 Dicerandra Species 0.000 claims 1
- 239000008257 shaving cream Substances 0.000 claims 1
- 239000011493 spray foam Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 8
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 abstract description 3
- 229920001577 copolymer Polymers 0.000 description 44
- 239000000243 solution Substances 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 26
- 238000009472 formulation Methods 0.000 description 22
- 125000000217 alkyl group Chemical group 0.000 description 20
- 210000003491 skin Anatomy 0.000 description 19
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 15
- 229960003237 betaine Drugs 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 12
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 12
- 229940048053 acrylate Drugs 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000002537 cosmetic Substances 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- 239000004205 dimethyl polysiloxane Substances 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- 239000000499 gel Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- 229920002472 Starch Polymers 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 235000019698 starch Nutrition 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 229920002678 cellulose Chemical class 0.000 description 7
- 239000001913 cellulose Chemical class 0.000 description 7
- 235000010980 cellulose Nutrition 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 7
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 7
- 239000008107 starch Substances 0.000 description 7
- 239000002562 thickening agent Substances 0.000 description 7
- 244000303965 Cyamopsis psoralioides Species 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229940008099 dimethicone Drugs 0.000 description 6
- 239000000834 fixative Substances 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 6
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 5
- 229920001661 Chitosan Polymers 0.000 description 5
- 229920002907 Guar gum Polymers 0.000 description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 235000010417 guar gum Nutrition 0.000 description 5
- 239000000665 guar gum Substances 0.000 description 5
- 229960002154 guar gum Drugs 0.000 description 5
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- OYINQIKIQCNQOX-UHFFFAOYSA-M 2-hydroxybutyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCC(O)C[N+](C)(C)C OYINQIKIQCNQOX-UHFFFAOYSA-M 0.000 description 4
- 244000215068 Acacia senegal Species 0.000 description 4
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- 229920000084 Gum arabic Polymers 0.000 description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 235000010489 acacia gum Nutrition 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 150000008051 alkyl sulfates Chemical class 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 230000003750 conditioning effect Effects 0.000 description 4
- 239000008406 cosmetic ingredient Substances 0.000 description 4
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- 239000006185 dispersion Substances 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 4
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- 239000004615 ingredient Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
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- LIFHMKCDDVTICL-UHFFFAOYSA-N 6-(chloromethyl)phenanthridine Chemical compound C1=CC=C2C(CCl)=NC3=CC=CC=C3C2=C1 LIFHMKCDDVTICL-UHFFFAOYSA-N 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 206010019049 Hair texture abnormal Diseases 0.000 description 3
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- 108010076876 Keratins Proteins 0.000 description 3
- 102000011782 Keratins Human genes 0.000 description 3
- 244000062730 Melissa officinalis Species 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000004280 Sodium formate Substances 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 239000011575 calcium Substances 0.000 description 3
- 230000003766 combability Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
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- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
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- RTVVXRKGQRRXFJ-UHFFFAOYSA-N sodium;2-sulfobutanedioic acid Chemical compound [Na].OC(=O)CC(C(O)=O)S(O)(=O)=O RTVVXRKGQRRXFJ-UHFFFAOYSA-N 0.000 description 3
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- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- DHVLDKHFGIVEIP-UHFFFAOYSA-N 2-bromo-2-(bromomethyl)pentanedinitrile Chemical compound BrCC(Br)(C#N)CCC#N DHVLDKHFGIVEIP-UHFFFAOYSA-N 0.000 description 2
- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 description 2
- ZKYCLDTVJCJYIB-UHFFFAOYSA-N 2-methylidenedecanamide Chemical compound CCCCCCCCC(=C)C(N)=O ZKYCLDTVJCJYIB-UHFFFAOYSA-N 0.000 description 2
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
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- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
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- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 description 1
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- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
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- GHTMQNZCRVHCQP-UHFFFAOYSA-J tetrasodium;4-[1,2-dicarboxyethyl(octadecyl)amino]-4-oxo-2-sulfobutanoate Chemical compound [Na+].[Na+].[Na+].[Na+].CCCCCCCCCCCCCCCCCCN(C(CC(O)=O)C(O)=O)C(=O)CC(C([O-])=O)S(O)(=O)=O.CCCCCCCCCCCCCCCCCCN(C(CC(O)=O)C(O)=O)C(=O)CC(C([O-])=O)S(O)(=O)=O.CCCCCCCCCCCCCCCCCCN(C(CC(O)=O)C(O)=O)C(=O)CC(C([O-])=O)S(O)(=O)=O.CCCCCCCCCCCCCCCCCCN(C(CC(O)=O)C(O)=O)C(=O)CC(C([O-])=O)S(O)(=O)=O GHTMQNZCRVHCQP-UHFFFAOYSA-J 0.000 description 1
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- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
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- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- GVPDNFYOFKBFEN-UHFFFAOYSA-N trimethyl(octadecoxy)silane Chemical compound CCCCCCCCCCCCCCCCCCO[Si](C)(C)C GVPDNFYOFKBFEN-UHFFFAOYSA-N 0.000 description 1
- UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 description 1
- UUJLHYCIMQOUKC-UHFFFAOYSA-N trimethyl-[oxo(trimethylsilylperoxy)silyl]peroxysilane Chemical compound C[Si](C)(C)OO[Si](=O)OO[Si](C)(C)C UUJLHYCIMQOUKC-UHFFFAOYSA-N 0.000 description 1
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- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
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- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8194—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5428—Polymers characterized by specific structures/properties characterized by the charge amphoteric or zwitterionic
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/369,044 US20070207106A1 (en) | 2006-03-06 | 2006-03-06 | Low molecular weight ampholytic polymers for personal care applications |
| US11/369,044 | 2006-03-06 | ||
| PCT/US2007/005630 WO2007103337A2 (en) | 2006-03-06 | 2007-03-06 | Low molecular weight ampholytic polymers for personal care applications |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2644146A1 CA2644146A1 (en) | 2007-09-13 |
| CA2644146C true CA2644146C (en) | 2013-04-23 |
Family
ID=38471682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2644146A Expired - Fee Related CA2644146C (en) | 2006-03-06 | 2007-03-06 | Low molecular weight ampholytic polymers for personal care applications |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US20070207106A1 (de) |
| EP (1) | EP1998744B1 (de) |
| JP (1) | JP5374163B2 (de) |
| KR (1) | KR20080109805A (de) |
| CN (1) | CN101442978B (de) |
| AU (1) | AU2007223999B2 (de) |
| BR (1) | BRPI0707077B1 (de) |
| CA (1) | CA2644146C (de) |
| EA (1) | EA200801872A1 (de) |
| ES (1) | ES2541312T3 (de) |
| MX (1) | MX2008011393A (de) |
| UA (1) | UA94933C2 (de) |
| WO (1) | WO2007103337A2 (de) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2394167T3 (es) * | 2006-10-16 | 2013-01-23 | Materials And Technologies Corporation | Aparato de procesamiento húmedo usando un menisco de fluído |
| MX2011009195A (es) * | 2009-03-20 | 2012-02-28 | Basf Se | Polimeros anfoliticos de secado rapido para composiciones de limpieza. |
| US20110177018A1 (en) | 2010-01-15 | 2011-07-21 | Paul Martin Lipic | Personal Care Compositions Comprising A Hydrophobically Modified Cationic Polysaccharide |
| US20110177017A1 (en) | 2010-01-15 | 2011-07-21 | Timothy Woodrow Coffindaffer | Non-Aerosol Personal Care Compositions Comprising A Hydrophobically Modified Cationic Polysaccharide |
| US9017652B1 (en) * | 2010-04-09 | 2015-04-28 | Lubrizol Advanced Materials, Inc. | Combination of crosslinked cationic and ampholytic polymers for personal and household applications |
| US20110259359A1 (en) | 2010-04-27 | 2011-10-27 | David Matthew Groh | Device For Dispensing A Personal Care Product |
| US20110272320A1 (en) | 2010-05-06 | 2011-11-10 | Ali Abdelaziz Alwattari | Aerosol Shave Composition Comprising A Hydrophobical Agent Forming At Least One Microdroplet |
| US20110274627A1 (en) | 2010-05-06 | 2011-11-10 | Ali Abdelaziz Alwattari | Method Of Making An Aerosol Shave Composition Comprising A Hydrophobical Agent Forming At Least One Microdroplet |
| CN102452096A (zh) | 2010-10-28 | 2012-05-16 | 吉列公司 | 用于分配液体的毛发移除装置的柄部 |
| CN102452094A (zh) | 2010-10-28 | 2012-05-16 | 吉列公司 | 分配液体的毛发移除套件 |
| WO2012058214A1 (en) | 2010-10-28 | 2012-05-03 | The Gillette Company | Applicator with a baffle for a hair removal device |
| CN102452092B (zh) | 2010-10-28 | 2015-04-01 | 吉列公司 | 分配液体的毛发移除装置 |
| CN102452095B (zh) | 2010-10-28 | 2014-10-29 | 吉列公司 | 用于分配液体的毛发移除装置的施用装置 |
| CN102452090A (zh) | 2010-10-28 | 2012-05-16 | 吉列公司 | 个人护理瓶 |
| CN102452091B (zh) | 2010-10-28 | 2015-08-12 | 吉列公司 | 用于毛发移除装置的具有导流板的施用装置 |
| CN102452089B (zh) | 2010-10-28 | 2015-01-14 | 吉列公司 | 具有细长凹槽的毛发移除刀片架 |
| CN102452088B (zh) | 2010-10-28 | 2015-07-01 | 吉列公司 | 具有刀片架保持覆盖件的毛发移除装置 |
| CN102452093A (zh) | 2010-10-28 | 2012-05-16 | 吉列公司 | 具有可移除的个人护理瓶的毛发移除装置 |
| CN102452085B (zh) | 2010-10-28 | 2016-01-27 | 吉列公司 | 用于分配液体的毛发移除装置的泵 |
| JP5832118B2 (ja) * | 2011-04-05 | 2015-12-16 | ライオン株式会社 | 粉体含有化粧料 |
| WO2013025891A1 (en) | 2011-08-16 | 2013-02-21 | The Gillette Company | An aerosol shave composition comprising a hydrophobical agent forming at least one microdroplet and an anti-irritation agent |
| JP2015040207A (ja) * | 2013-08-23 | 2015-03-02 | 東邦化学工業株式会社 | 低分子量両性共重合体を含む毛髪処理用組成物 |
| WO2015143997A1 (en) * | 2014-03-26 | 2015-10-01 | The Procter & Gamble Company | Cleaning compositions containing cationic polymers, and methods of making and using same |
| CN104910325B (zh) * | 2015-06-30 | 2017-03-29 | 广州天赐高新材料股份有限公司 | 水溶性两性离子聚合物及其制备方法 |
| CN117003931A (zh) * | 2023-09-01 | 2023-11-07 | 中国石油化工股份有限公司 | 一种超低分子量两性螯合剂及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2438091A (en) * | 1943-09-06 | 1948-03-16 | American Cyanamid Co | Aspartic acid esters and their preparation |
| US2528378A (en) * | 1947-09-20 | 1950-10-31 | John J Mccabe Jr | Metal salts of substituted quaternary hydroxy cycloimidinic acid metal alcoholates and process for preparation of same |
| US2658072A (en) * | 1951-05-17 | 1953-11-03 | Monsanto Chemicals | Process of preparing amine sulfonates and products obtained thereof |
| US3769398A (en) * | 1970-05-25 | 1973-10-30 | Colgate Palmolive Co | Polyethylenimine shampoo compositions |
| PL167653B1 (pl) * | 1990-12-05 | 1995-10-31 | Procter & Gamble | Ciekla, szamponowa kompozycja pielegnacyjna do wlosów PL PL |
| NZ243275A (en) * | 1991-06-28 | 1995-03-28 | Calgon Corp | Hair care compositions comprising ampholytic terpolymers |
| NZ243273A (en) * | 1991-06-28 | 1995-02-24 | Calgon Corp | Hair care compositions comprising ampholytic terpolymers |
| NZ243274A (en) * | 1991-06-28 | 1994-12-22 | Calgon Corp | Hair care compositions containing ampholytic terpolymers |
| US5338541A (en) * | 1992-10-15 | 1994-08-16 | Calgon Corporation | Dual cationic terpolymers providing superior conditioning properties in hair, skin and nail care products |
| US6210689B1 (en) * | 1998-03-18 | 2001-04-03 | National Starch & Chemical Co. Investment Holding Corporation | Keratin treating cosmetic compositions containing amphoteric polysaccharide derivatives |
| US6437185B1 (en) * | 1999-06-16 | 2002-08-20 | Finetex, Inc. | Quaternary ammonium compounds and process for preparing and using same |
| AU6404100A (en) * | 1999-07-16 | 2001-02-05 | Calgon Corporation | Water soluble polymer composition and method of use |
| GB0027978D0 (en) | 2000-11-16 | 2001-01-03 | Ciba Sc Holding Ag | High solids solution of a cationic copolymer |
| FR2849774B1 (fr) * | 2003-01-15 | 2007-01-19 | Eugene Perma France | Composition pur la coloration permanente de fibres keratiniques. |
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2006
- 2006-03-06 US US11/369,044 patent/US20070207106A1/en not_active Abandoned
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2007
- 2007-03-06 EP EP07752342.1A patent/EP1998744B1/de active Active
- 2007-03-06 BR BRPI0707077A patent/BRPI0707077B1/pt active IP Right Grant
- 2007-03-06 MX MX2008011393A patent/MX2008011393A/es active IP Right Grant
- 2007-03-06 JP JP2008558341A patent/JP5374163B2/ja not_active Expired - Fee Related
- 2007-03-06 CN CN2007800080396A patent/CN101442978B/zh active Active
- 2007-03-06 CA CA2644146A patent/CA2644146C/en not_active Expired - Fee Related
- 2007-03-06 WO PCT/US2007/005630 patent/WO2007103337A2/en not_active Ceased
- 2007-03-06 ES ES07752342.1T patent/ES2541312T3/es active Active
- 2007-03-06 AU AU2007223999A patent/AU2007223999B2/en not_active Ceased
- 2007-03-06 EA EA200801872A patent/EA200801872A1/ru unknown
- 2007-03-06 KR KR1020087024193A patent/KR20080109805A/ko not_active Ceased
- 2007-06-03 UA UAA200810699A patent/UA94933C2/ru unknown
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2009
- 2009-08-03 US US12/534,221 patent/US8658145B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP1998744A4 (de) | 2012-09-26 |
| US20090291053A1 (en) | 2009-11-26 |
| JP2009532335A (ja) | 2009-09-10 |
| CA2644146A1 (en) | 2007-09-13 |
| JP5374163B2 (ja) | 2013-12-25 |
| UA94933C2 (ru) | 2011-06-25 |
| ES2541312T3 (es) | 2015-07-17 |
| AU2007223999A1 (en) | 2007-09-13 |
| WO2007103337A2 (en) | 2007-09-13 |
| MX2008011393A (es) | 2008-10-22 |
| WO2007103337A3 (en) | 2007-11-22 |
| BRPI0707077B1 (pt) | 2016-03-15 |
| EP1998744A2 (de) | 2008-12-10 |
| EA200801872A1 (ru) | 2009-02-27 |
| CN101442978A (zh) | 2009-05-27 |
| KR20080109805A (ko) | 2008-12-17 |
| BRPI0707077A2 (pt) | 2011-04-19 |
| CN101442978B (zh) | 2013-03-13 |
| EP1998744B1 (de) | 2015-06-10 |
| US20070207106A1 (en) | 2007-09-06 |
| AU2007223999B2 (en) | 2012-08-09 |
| US8658145B2 (en) | 2014-02-25 |
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